


It Hurts Like This (Please Help Me)

by ivegotissuesyo



Category: The Umbrella Academy (TV)
Genre: Angst, Creepy The Handler (Umbrella Academy), Dead Dove: Do Not Eat, Desperation Play, Extremely Dubious Consent, F/M, Hand Jobs, Hurt No Comfort, Hurt Number Five | The Boy, Non-Consensual Drug Use, Non-Consensual Touching, Not Beta Read, Number Five | The Boy Whump, Omorashi, PLEASE HEED TAGS, Public Sex, Rape/Non-con Elements, Sexual Content, The Author Regrets Everything, Watersports, Wetting
Language: English
Status: Completed
Published: 2020-11-14
Updated: 2020-11-14
Packaged: 2021-03-09 19:00:41
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 1,170
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27551170
Author URL: https://archiveofourown.org/users/ivegotissuesyo/pseuds/ivegotissuesyo
Summary: Please Heed Tags.The Handler gets her hands on Five, gets her fingers under his skin, gets her teeth into his heart. He's her property, now. And there's nothing Five can do about it.Dead Dove: Do Not Eat. Use Caution.
Relationships: Number Five | The Boy/The Handler (Umbrella Academy)
Comments: 13
Kudos: 84





	It Hurts Like This (Please Help Me)

**Author's Note:**

> Please heed the tags and warnings. This is your last warning. This fic contains rape/sexual assault, noncon drug use, noncon sexual assault, and underage sexual assault.

She has his cock in her hand. It's small, a gentle weight that fits near-fully in her palm. As the Handler strokes in long, smooth glides, Five keens against her, shifting weakly in her lap. The concoction they injected him with worked beautifully, it seems, as his powers sputter and give out every few seconds. His head is tilted back, resting on her shoulder, letting her hear all his breathy moans closely. Her heart flutters with excitement, a heat building in her stomach and between her legs as she works his cock to hardness.

Five's hand sluggishly falls to her moving wrist. He swallows thickly, his throat bobbing. The Handler coos.

"Now, now, Five. Be a good boy. I  _ know _ you're enjoying this." She cranes her neck to kiss his jaw. He makes to recoil, she knows, but the lag from the drug turns the movement into a flimsy flinch. Oh, if only he could fight back against her. She loves a good challenge, and Five always aims to deliver, even if he doesn't know it. He takes and takes and she wants to give and give; give him fuel to hate her, give him matches to ignite his flame. Being able to one day see him feral, battling for his life, for his  _ dignity _ as she slides a cock deep inside him, the thought makes her hum.

Though, the Handler must admit: there is something so endearing, so  _ hot _ about Five being completely incapacitated in her grasp.

It reminds her of their time in Cairo together, back when he was in his older, more mature body. While unconscious from a head injury, she rode him to completion, moving him however she wanted. He was malleable but far from adorable.

Not as he is  _ now _ , writhing against her.

The Handler snakes her free hand under his sweater vest and button up shirt, brushing over his heaving stomach, his burning skin. Thankfully, she discarded his blazer, shoes, and tie on the other side of the room. They would get in the way, because Five is so  _ warm _ , so soft, like a doll in his younger form, and she is  _ drowning _ in it.

His cock twitches in her hand, drooling precome. It's adorable, flushed pink, like a hand-held heater. She chuckles at the thought, moving to press another kiss to his jaw. Her tongue works against his plush skin, biting and kicking a stripe up to his earlobe. Five shudders quietly.

The hand he has around her wrist tightens only just, an attempt to save face, perhaps, or perhaps it's because his breath is picking up, his heart is skittering under her palm: he's about to come.

"Go ahead," she whispers against his neck. "Come, Five. Come for me-"

She doesn't get to finish her sentence as he goes tense, a sweet sound scraping up his throat as he comes in her hand. It dribbles hot in-between her fingers, already beginning to cool from where it spattered on his shorts.

The Handler bites his neck again, just below his jaw. "Good boy."

Five deflates against her. His breaths come deeply, head head lolling on her shoulder. He lets his eyes slip shut, and the Handler can't help but sigh, a swell of adoration in her heart.

They're far from done.

He's still hard, after all.

She gives his cute little cock a firm stroke. 

Five hisses. He opens his mouth, as if he's going to say something, but nothing comes out. The Handler begins to work him again, jerking him off faster this time. If she can wring a couple of orgasms from him while the drug is still effective, she'll be pleased enough. Naturally, the Handler wants nothing more than to humiliate him indefinitely, being the only one to give him both pleasure and pain, but alas. The drug will wear off eventually, she knows.

So, she might as well have fun while she can.

The hand pressed to his stomach trails upwards, up his warm chest. She finds a nipple and pinches, gently, tugging at it to hardness. Her other fingers work fast, her wrist twisting expertly to bring him to the edge within minutes. Pubescent boys are so sensitive, and it is endearing to see Five teetering on yet another orgasm so quickly.

She bruises the hinge of his jaw with a sucking kiss. "You want another one, Five? Want to come again."

This time, he manages to grind out, "G-Go fuck yours-self." His voice cracks halfway through. Five shivers hard. His hand around her wrist tightens near painfully so, a slight pinching from his nails.

The Handler frowns.

Perhaps the concoction is leaving his body faster than she anticipated?

Five chokes out, "S-Stop.  _ Wait. _ "

She smiles. "You know I can't do that, Five."

His eyes narrow in embarrassment. A flush reddens his cheeks. "Jesus Christ, just  _ stop. _ "

"Why?" she asks. Her fingers rub at his other nipple. His breathing tightens once more. "Tell me why and I may consider it."

"I-" He gets tangled in his pride. The Handler furthers her strokes, urging him towards his second orgasm. He stiffens against her as he growls, "I- _ Fuck _ , I n-need to piss. Just  _ stop. _ "

She does.

It would be inconvenient if he soiled her skirt, after all. It cost her quite a bit, and while she had plenty of money to purchase another, she doesn't see the appeal to him urinating on her like a dog.

But him urinating  _ on the floor? _

Like the good dog he is?

The Handler proceeds her handjob, though slower, letting Five ride his edge. He curses under his breath. Both his hands fly to her own, prying at the fingers wrapped around his cock. " _ Stop. _ " he breathes.

"No." she says.

Shifting them forward, the Handler maneuvers him to the end of her knees, sliding him back and bracketing her free hand over his chest, pinning him to her. His head flops limp against her collarbone, forehead sweaty at the crook of her neck. He looks tense, brows pinched, as she continues to jerk him off.

"Go ahead, then, Five." She angles his cock away from them. "Let it _all_ out."

"F-" Five chokes back yet another whine.

He spasms against her as he comes for a second time, spilling over her hand, over his shorts, over the floor. She stops stroking. A moment later, she feels the urine work up his softening cock, dribbling to her office floor.

Five turns into her. His grip tightens on her arm. The poor thing must have been humiliated, but the Handler couldn't keep herself from feeling weightless in the high of the situation. Her little assassin, pissing himself from being played with too much; it was  _ encapsulating _ to think about.

"Good boy." the Handler says. She rests her chin on his sweaty temple. "Take a breath, Five." He does. The Handler's lips curl into a smile. She doesn't say a word, merely waiting for his urine stream to stop before beginning to jerk his cock again.

**Author's Note:**

> This was written out of spite and in the midst of flashbacks. Thank you for reading, and sorry for subjecting you to my mind.
> 
> Please don't attack me, thanks. I'm working through stuff.
> 
> Hope you found it enjoyable or hot or disturbing or whatever floats your boat. Keep an eye out for more of my messed up content in the future. :)


End file.
